Ethanolamine → HCID 59593538, compound

HRID 2261463Notes

Reaction equation

HRID 2261463 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10](=[O:23])[C:11]2[S:18][C:17]([CH3:19])=[C:16]3[C:12]=2[CH2:13][C@H:14]2[C:20]([CH3:22])([CH3:21])[C@H:15]23)[CH:5]=[C:4]([CH3:24])[C:3]=1[CH2:25][CH2:26][C:27]([OH:29])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:61]([CH2:63][NH2:64])[OH:62]>CN(C=O)C.C(#N)C.C(O)=O>[CH3:24][C:4]1[CH:5]=[C:6]([CH2:8][CH2:9][C:10](=[O:23])[C:11]2[S:18][C:17]([CH3:19])=[C:16]3[C:12]=2[CH2:13][C@H:14]2[C:20]([CH3:22])([CH3:21])[C@H:15]23)[CH:7]=[C:2]([CH3:1])[C:3]=1[CH2:25][CH2:26][C:27]([NH:64][CH2:63][CH2:61][OH:62])=[O:29]

Participants

8

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59593534HCID 59593534, compound

Product 1

HCID 59593538HCID 59593538, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenyl}-propionic acid (10 mg, 22 μmol) in DMF (0.5 mL), TBTU (8 mg, 24 μmol) and DIPEA (10 mg, 72.6 μmol) is added. The mixture is stirred at rt for 5 min before ethanolamine (7 mg, 110 μmol) is added. Stirring is continued for 16 h at rt. The mixture is diluted with acetonitril (0.5 mL) and formic acid (25 μL) and separated by prep. HPLC (Waters SymmetryC18 19×50 mm 5 μm, 80% to 0% water (0.5% HCOOH) in acetonitrile) to give 3-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenyl}-N-(2-hydroxy-ethyl)-propionamide (7 mg) as a colourless resin; LC-MS: tR=1.03 min, [M+1]+=454.35.

Workup

  1. additionis added
  2. customseparated by prep

Sources & evidence

ORD record
ord-27a1ad7c29494bfd846cc81e345a32ff
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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